Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 106 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 2Deluxe Sail & Snorkel to the Captain Cook Monument
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters a... More

Deluxe Sail & Snorkel to the Captain Cook Monument
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Hawaii
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Superb505 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun
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Hawaii
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Superb152 reviews4.8
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
Molokini Snorkel and Performance Sail from Ma'alaea Harbor
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More

Molokini Snorkel and Performance Sail from Ma'alaea Harbor
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Hawaii
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Superb204 reviews4.9
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views o... More

Honolulu Sunset Sail from Kewalo Harbor Including Drinks
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Hawaii
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Superb137 reviews4.9
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
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Hawaii
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Superb35 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
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Hawaii
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Superb241 reviews4.8
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets. Snorkel calm waters and lush coral gardens u... More

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
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Hawaii
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Superb659 reviews5
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....
Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming
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Hawaii
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Superb168 reviews5
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....
Waikiki Sunset Boat Cruise
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More

Waikiki Sunset Boat Cruise
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Hawaii
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Superb43 reviews5
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....
Snorkel with Manta Rays Guaranteed
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Snorkel with Manta Rays Guaranteed
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Hawaii
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Superb728 reviews4.8
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty of interesting whale information Convenient location walking... More

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
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Hawaii
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Superb147 reviews4.7
Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well a....
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)... More

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
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Hawaii
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Superb261 reviews4.8
-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel....
Sunset Cocktail Cruise from Anaeho'omalu Bay
Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More

Sunset Cocktail Cruise from Anaeho'omalu Bay
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Hawaii
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Superb59 reviews4.8
Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....
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Hawaii
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Superb923 reviews4.7
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....
Luxury Catamaran Whale Watch
From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More

Luxury Catamaran Whale Watch
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Hawaii
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Superb40 reviews5
From December through April, the waters off Maui come alive with the sights and sounds of the majest....
Deluxe Sail & Snorkel to the Captain Cook Monument
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters... More

Deluxe Sail & Snorkel to the Captain Cook Monument
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Hawaii
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Superb461 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
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Hawaii
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Superb233 reviews4.9
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....
2-Hour Oahu Sunset Catamaran Sail
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for... More

2-Hour Oahu Sunset Catamaran Sail
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Hawaii
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Superb108 reviews4.9
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran f....

Kona Tradewind Catamaran Day Sail
Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunning Kona coastline. This relaxing daytime cruise is perfect for spotting Hawaii’s incredible marine wildlife—keep your eyes peel... More
Free Cancellation
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Kona Tradewind Catamaran Day Sail
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Hawaii
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Superb37 reviews4.8
Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunnin....
Free Cancellation
(Saving 16% )
Sunset and Manta Ray Snorkel Adventure
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays! Upon arriving, receive an in... More

Sunset and Manta Ray Snorkel Adventure
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Hawaii
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Superb800 reviews4.9
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....